Total Synthesis of Hinduchelins A-D, Stereochemical Revision of Hinduchelin A, and Biological Evaluation of Natural and Unnatural Analogues.
J Org Chem
; 84(10): 6459-6464, 2019 05 17.
Article
em En
| MEDLINE
| ID: mdl-31039303
ABSTRACT
Here, we report the first total synthesis of hinduchelins A-D, a family of nontoxic catechol derivatives from Streptoalloteichus hindustanus, possessing a druglike chemotype and modest iron-chelating ability. A concise synthesis was developed employing methyl 5-methyloxazole-4-carboxylate as a single starting material to provide hinduchelins A-D (and unnatural analogues) in only four steps and 5-15% overall yields; moreover, the stereochemistry of hinduchelin A was reassigned from ( S) to ( R). Biological evaluation confirmed that natural and unnatural hinduchelins are weak iron chelators (siderophores).
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Base de dados:
MEDLINE
Assunto principal:
Catecóis
/
Quelantes de Ferro
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article